N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Base Information

Chemical Name:N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide
CAS No.:245523-32-4
Molecular Formula:C₅₄H₅₉N₅O₄Si
Molecular Weight:870.179
Hs Code.:

Synonyms:N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

There total 17 articles about N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

: 245523-29-9
N-Triphenylmethyl (3S)-3-{N'-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl]-N'-[(1R)-1-bromo-2-methylpropylcarbonyl]amino}-4-(tert-butyldiphenylsilyloxy)butyramide

: 245523-32-4
N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: With potassium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 0.916667h;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

: 54966-42-6,1466-22-4
ethyl 3-benzylacrylate

: 245523-32-4
N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 11 steps

1: 81 percent / DIBAL-H / CH₂Cl₂ / 1 h / -78 °C

2: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 °C

3: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating

4: collidine / CH₂Cl₂ / 18 h / -78 - 20 °C

5: CH₂Cl₂ / 24 h / 0 - 20 °C

6: 80 percent / NaOMe / tetrahydrofuran / 0.25 h / 20 °C

7: 66 percent / ethanol / 96 h / Heating

8: 91 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

9: DIC / CH₂Cl₂ / 4 h / 0 °C

10: HCl; H₂O / tetrahydrofuran / 96 h / 20 °C

11: 69 percent / KH / tetrahydrofuran; dimethylformamide / 0.92 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; water; sodium methylate; potassium hydride; diisobutylaluminium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Epoxidation / 3: Ring cleavage / 4: Acylation / 5: Substitution / 6: Epoxidation / 7: Alkylation / 8: Etherification / 9: Acylation / 10: Hydrolysis / 11: Cyclization;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L

Reference yield:

: 42238-15-3,22910-59-4,49676-93-9
(2E)-4-phenylbut-2-en-1-ol

: 245523-32-4
N-Triphenylmethyl (3S)-3-{(2S,6S)-6-[(1S)-1-azido-2-phenylethyl]-2-isopropylmorpholin-3-one-4-yl}-4-(tert-butyldiphenylsilyloxy)butyramide

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / Ti(OiPr)4; tBuOOH; D-(-)-diethyl tartrate / CH₂Cl₂ / 24 h / -20 °C

2: 95 percent / Ti(OiPr)2(N₃)2 / benzene / 0.5 h / Heating

3: collidine / CH₂Cl₂ / 18 h / -78 - 20 °C

4: CH₂Cl₂ / 24 h / 0 - 20 °C

5: 80 percent / NaOMe / tetrahydrofuran / 0.25 h / 20 °C

6: 66 percent / ethanol / 96 h / Heating

7: 91 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

8: DIC / CH₂Cl₂ / 4 h / 0 °C

9: HCl; H₂O / tetrahydrofuran / 96 h / 20 °C

10: 69 percent / KH / tetrahydrofuran; dimethylformamide / 0.92 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; 2,3,5-trimethyl-pyridine; hydrogenchloride; tert.-butylhydroperoxide; diethyl (2S,3S)-tartrate; diisopropoxytitanium diazide; water; sodium methylate; potassium hydride; dacarbazine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 1: Epoxidation / 2: Ring cleavage / 3: Acylation / 4: Substitution / 5: Epoxidation / 6: Alkylation / 7: Etherification / 8: Acylation / 9: Hydrolysis / 10: Cyclization;
DOI:10.1002/(SICI)1521-3765(19990802)5:8<2241::AID-CHEM2241>3.0.CO;2-L